7367-87-5

Basic information

• Product Name: methyl 3-hydroxyoctanoate
• Synonyms: 3-Hydroxycaprylic acid methyl ester;3-Hydroxyoctanoic acid methyl ester
• CAS NO: 7367-87-5
• Molecular Formula: C₉H₁₈O₃
• Molecular Weight: 174.24
• EINECS: 230-917-3
• Product Categories: Aliphatics;Miscellaneous Reagents;Aliphatics, Miscellaneous Reagents
• Mol File: 7367-87-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 259.9 °C at 760 mmHg
• Flash Point: 102.2 °C
• Appearance: /
• Density: 0.976 g/cm³
• Vapor Pressure: 0.00184mmHg at 25°C
• Refractive Index: 1.439
• PKA: 14.09±0.20(Predicted)
• CAS DataBase Reference: methyl 3-hydroxyoctanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-hydroxyoctanoate(7367-87-5)
• EPA Substance Registry System: methyl 3-hydroxyoctanoate(7367-87-5)

Safety Data

• Hazardous Substances Data: 7367-87-5(Hazardous Substances Data)

Usage

Description

Methyl 3-hydroxyoctanoate, also known as 3-hydroxyoctanoic acid methyl ester, is a volatile ester that is naturally found in fruit juices. It is characterized by its distinct fruity aroma and is commonly used in the flavor and fragrance industry due to its pleasant scent.

Uses

Used in Flavor and Fragrance Industry:
Methyl 3-hydroxyoctanoate is used as a flavoring compound for its fruity aroma, enhancing the taste and smell of various food and beverage products. It is particularly favored for its ability to add a natural, fresh fruit flavor to products without altering their other sensory attributes.
Used in Cosmetics and Personal Care Industry:
In the cosmetics and personal care industry, methyl 3-hydroxyoctanoate is used as a fragrance ingredient to provide a pleasant and long-lasting scent to products such as perfumes, lotions, and shampoos. Its natural origin and fruity aroma make it a popular choice for creating appealing and sophisticated fragrances in these products.
Used in the Food and Beverage Industry:
Methyl 3-hydroxyoctanoate is also utilized in the food and beverage industry as an additive to impart a fruity flavor to products such as soft drinks, candies, and baked goods. Its natural occurrence in fruit juices makes it a suitable choice for adding a fresh and authentic taste to these products without the need for artificial flavorings.

InChI:InChI=1/C9H18O3/c1-3-4-5-6-8(10)7-9(11)12-2/h8,10H,3-7H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 1038622-41-1 4-hydroxy-2-nonanone 
• 102368-24-1 (S)-4-hydroxyl-2-nonenone 
• 22348-95-4 methyl 3-oxooctanoate 
• 33796-86-0 3-hydroxyoctanoic acid 
• 485-80-3 S-adenosyl-L-methionine 
• 142-61-0 Hexanoyl chloride 
• 56830-24-1 Methyl-3-methoxyoctanoat 
• 10488-95-6 ethyl 3-oxooctanoate 
• 132377-81-2 (2S*,3R*)-methyl 2,3-dihydroxyoctanoate 
• 79-20-9 acetic acid methyl ester 
• 66-25-1 hexanal 
• 132377-77-6 (2R*,3R*)-methyl 2-bromo-3-hydroxyoctanoate 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 35234-21-0 methyl 3-(acetoxy)octanoate 
• 22348-95-4 methyl 3-oxooctanoate 
• 7367-81-9 methyl (E)-oct-2-enoate 
• 66997-64-6 (S)-methyl 3-hydroxyoctanoate 
• 78672-90-9 methyl (R)-(-)-3-hydroxydecanoate 
• 33796-86-0 3-hydroxyoctanoic acid 

Relevant articles and documents

Fungal metabolism of trans 2 octenoic acid

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Polyhydroxyalkanoate-based 3-hydroxyoctanoic acid and its derivatives as a platform of bioactive compounds

A library of 18 different compounds was synthesized starting from (R)-3-hydroxyoctanoic acid which is derived from the bacterial polymer polyhydroxyalkanoate (PHA). Ten derivatives, including halo and unsaturated methyl and benzyl esters, were synthesized and characterized for the first time. Given that (R)-3-hydroxyalkanoic acids are known to have biological activity, the new compounds were evaluated for antimicrobial activity and in vitro antiproliferative effect with mammalian cell lines. The presence of the carboxylic group was essential for the antimicrobial activity, with minimal inhibitory concentrations against a panel of bacteria (Gram-positive and Gram-negative) and fungi (Candida albicans and Microsporum gypseum) in the range 2.87.0 mM and 0.16.3 mM, respectively. 3-Halogenated octanoic acids exhibited the ability to inhibit C. albicans hyphae formation. In addition, (R)-3-hydroxyoctanoic and (E)-oct-2-enoic acids inhibited quorum sensing-regulated pyocyanin production in the opportunistic pathogen Pseudomonas aeruginosa PAO1. Generally, derivatives did not inhibit mammalian cell proliferation even at 3-mM concentrations, while only (E)-oct-2-enoic and 3-oxooctanoic acid had IC50 values of 1.7 and 1.6 mM with the human lung fibroblast cell line.

Biochemical Studies of Mycobacterial Fatty Acid Methyltransferase: A Catalyst for the Enzymatic Production of Biodiesel

Summary Transesterification of fatty acids yields the essential component of biodiesel, but current processes are cost-prohibitive and generate waste. Recent efforts make use of biocatalysts that are effective in diverting products from primary metabolism to yield fatty acid methyl esters in bacteria. These biotransformations require the fatty acid O-methyltransferase (FAMT) from Mycobacterium marinum (MmFAMT). Although this activity was first reported in the literature in 1970, the FAMTs have yet to be biochemically characterized. Here, we describe several crystal structures of MmFAMT, which highlight an unexpected structural conservation with methyltransferases that are involved in plant natural product metabolism. The determinants for ligand recognition are analyzed by kinetic analysis of structure-based active-site variants. These studies reveal how an architectural fold employed in plant natural product biosynthesis is used in bacterial fatty acid O-methylation. Mycobacterial fatty acid methyltransferases are employed as biocatalysts for the production of biodiesel. Petronikolou and Nair describe structural and biochemical characterization of a mycobacterial fatty acid methyltransferase, reveal an unexpected homology to enzymes involved in plant primary metabolism, and provide insights into substrate preference.